Meet the Woman Helping Men Walk on the Wildside
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Meet the Woman Helping Men Walk on the Wildside

Toronto's Patricia “Paddy” Aldridge has been providing cross-dressing men a safe place to transform for more than two decades.

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Wildside customer Sabrina checks out her new wig in the mirror.

In 1987, an ex-stripper and theatre school grad with a flair for makeup and costuming put an ad in NOW Magazine. “Take a walk on the Wildside,” it read. “Who’s that girl? It could be you.” Her phone rang off the hook.

Thirty years later, Patricia “Paddy” Aldridge is still helping men transform from he to she at Wildside, her Gerrard Street East boutique that provides a safe, non-judgemental space for Toronto’s cross-dressing and transitioning communities. And this weekend, a short documentary film about Wildside is making its world premiere at the Hot Docs film festival

Take a Walk on the Wildside offers viewers a peek through the windows of the city’s oldest cross-dressing store, exploring the varied reasons why Aldridge’s clients cross-dress and why, in the age of online shopping, this bricks-and-mortar shop is still relevant.

Director and writer Lisa Rideout had lived in Toronto for over a decade, but hadn’t known Wildside existed. One day she went into the store to scout it as a possible location for another film.

“When Lisa came in,” Aldridge says, “I said, ‘Don’t you want to do a movie? Nobody’s ever told the true story.’ And Lisa said, ‘Oh I could do that.’”

After graduating from Ryerson Theatre School, then building a float and designing costumes for the Santa Claus Parade, Aldridge had some down time. “I had lots of friends who were drag queens—I was a stripper, and we all looked the same as drag queens—and one said, ‘You know, there’s heterosexual guys that cross dress.’ So I put an ad in the paper,” she says.

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Wildside owner Patricia “Paddy” Aldridge.

She learned on the job. “People would call me and I would say, ‘I do makeup and I have some costumes for you to wear.’” Aldridge performed her transformations in her living room. “And then we would just talk,” she says. “I was like a psychiatrist, I guess.”

“When I started, I knew I didn’t know anything,” Aldridge says. “I didn’t know the difference between a transvestite and a transsexual and I wondered how am I gonna pull this off.”

In 1989, she sold her house and moved to the U.S. for a year to meet people in the cross-dressing community. She also found suppliers of everything from larger-sized clothing and shoes, to wigs, to “eyelashes, fingernails, and tits.”

On her return to Canada, the business grew so fast that she had to keep up-sizing, eventually landing in 1993 at her current Gerrard Street location.

“It was like a zeitgeist,” Aldridge says. The Canadian Crossdressers’ Club she and her then-partner started grew to 400 members. Like a wardrobe supervisor maintaining costumes for theatre actors, Aldridge stored wardrobes for club members. “They’d all put their ‘boy clothes’ in the locker, and then there’d be, like, 40 guys getting all dressed up.”

After several hours of make up and dressing, “I would take 20 newbies to dinner,” Aldridge says. “And some of them couldn’t walk in heels, and they’d be getting their lipstick all over their face, and their wigs would be falling off, and their corsets would be too tight.”

“It was fun, and innocent, and crazy in the 90s.”

Fun and innocent are words Aldridge uses when asked why people cross-dress. “It’s fun. It’s totally innocent. It’s just a fun thing.”

Rideout adds that when she tells people she’s made a film about cross-dressing, that’s one of the first questions she’s asked. “It’s almost like people want one answer,” she says. But what she learned through making the film is that there are a multitude of reasons. “Paddy made it very clear to me that one person does one thing, one person does another,” she says.

“I don’t think [cross-dressers] have a huge deal of representation in media, or when they are represented, that one person has a certain reason why they’re doing it. And that cannot represent an entire community.”

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Paddy helps one of her longtime customers, Ralph, get ready for a special occasion.

As Renee, an original Wildside customer who still visits from Silicon Valley once every five years says, “We are a highly unique group of people with a common bond of self expression through femininity.”

“For both Paddy and I,” Rideout says, “that was important to showcase in the film.”

The connection between the two women has inspired them to try to get a feature-length documentary off the ground. As Rideout explains, additional running time would allow viewers more than just a glimpse into the community, and the opportunity to learn more of Aldridge’s life story (the highs and lows of which include alcoholism and recovery, workaholism, surviving cancer, the deaths of dear friends, and two marriages) and what she does outside the store (everything from painting, running a gallery, filmmaking, to singing karaoke in a seniors’ home).

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Paddy and Take a Walk on the Wildside director/writer Lisa Rideout (centre) discuss a scene.

In the meantime, Rideout hopes that her short helps audiences recognize that human connection and community are still important, and that it demystifies and humanizes cross-dressers and shows off their individuality. “A cross-dresser is anyone. It could be a family member, a friend. And they do it for a variety of reasons, because they are humans.”

And what does Aldridge hope audiences take away? “Just be more tolerant. Accept the whole of society.”

Aldridge’s acceptance and encouragement inspires trust. For some clients, Aldridge is the only person they have told about their desire to cross-dress. “Imagine trying to tell somebody who didn’t want you to do that,” she says. “I listen. I give everybody a completely open field to talk about whatever it is that’s bothering them.”

“One of the initial questions I had was, can the store still exist in a time where people can go online and buy everything? They can go on YouTube and look up how to do their makeup,” says Rideout.

“But what can’t be provided online is this intimate relationship between two people. That’s what I found behind the doors. That’s the story we try to tell in the film.”

Take a Walk on the Wildside screens with the feature Grey Violet: Odd One Out on Saturday, April 29, and Monday, May 1. For Hot Docs tickets, visit the Festival’s online box office.